Benzene, 1-iodo-3-(trifluoromethyl)- → 2,2-Difluoro-1-[3-(trifluoromethyl)phenyl]-1-propanone

HRID 2371079Notes

Reaction equation

CC([Mg]Cl)C.I[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1.[F:17][C:18]([F:26])([CH3:25])[C:19](N(OC)C)=[O:20]>C1COCC1>[F:17][C:18]([F:26])([CH3:25])[C:19]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)=[O:20]

Participants

Conditions

Temperature: -15 °C

Procedure

A solution of 2-propylmagnesium chloride in THF (1.3 M, 7.5 ml) was cooled to −15° C. and admixed with 1-iodo-3-(trifluoromethyl)benzene (2.80 g, 10.2 mmol). The reaction mixture was stirred at −15° C. for 1 h, warmed to room temperature and admixed dropwise with a solution of 2,2-difluoro-N-methoxy-N-methylpropanamide (1.43 g, 9.35 mmol: prepared according to Synth. Comm. 2008 (38), 1940-1945), and stirred at room temperature overnight. Then the mixture was added to ice-cold dilute hydrochloric acid and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by means of silica gel chromatography with the eluent cyclohexane/ethyl acetate (EA) (0% FA to 30% EA).

Workup

temperaturewarmed to room temperature
stirringstirred at room temperature overnight
additionThen the mixture was added to ice-cold dilute hydrochloric acid
extractionextracted with ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulphate
concentrationconcentrated under reduced pressure
customThe residue was purified by means of silica gel chromatography with the eluent cyclohexane/ethyl acetate (EA) (0% FA to 30% EA)

Sources & evidence

ORD record: ord-74d2ad7d73b6436c9d6cb8c5a19ab26e
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710242B2

Reaction notes

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